Guest Stars Aasha Davis as Various Characters Bennie Arthur as Various Characters David Wain as Himself (Narrator) John Levenstein as Himself (Narrator) Ashley Barnhill as Herself (Narrator) Sam Richardson as Jim Brown Ron Funches as Herbert Muhammad Echo Kellum as Lew Alcindor Mary Elizabeth Ellis as Dorothy Fuldheim Gaius Charles as Muhammad Ali George Wallace as Bill Russell Lauren Sivan as Barbara Walters Samm Levine as Wayne Wheeler Aidan Sussman as Young Wayne Wheeler